Tetrahydrofuran → HCID 22503419, compound

HRID 1251194Notes

Reaction equation

HRID 1251194 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11](Cl)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][CH:4]=1.[Cl-].[NH4+].O1CCC[CH2:23]1>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH3:23])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinoline

Product 1

HCID 22503419HCID 22503419, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 178418745HCID 178418745, compoundCatalyst

Procedure

3-(4-Methoxyphenyl)-1-chloroisoquinoline (3.25 g) was dissolved in tetrahydrofuran (30 ml), followed by the addition of 3.0M ethylmagnesium bromide diethyl ether solution (12 ml) and NiCl2(dppp) (50 mg) at 0° C. After the mixture was reacted overnight at room temperature, the resulting reaction solution was poured into an aqueous solution of saturated ammonium chloride and extracted with ethyl acetate. The resulting organic layer was washed with water and brine, dried and evaporated, to give 3-(4-methoxyphenyl)-1-methylisoquinoline as an oil (3.3 g, yield; 100%).

Workup

  1. customAfter the mixture was reacted overnight at room temperature
  2. customthe resulting reaction solution
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with water and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-e51c724bffd843af99bf2994a09b23f5
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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